CN103805166A - Benzanthracene organic luminescent material, and preparation method and application thereof - Google Patents
Benzanthracene organic luminescent material, and preparation method and application thereof Download PDFInfo
- Publication number
- CN103805166A CN103805166A CN201210457318.3A CN201210457318A CN103805166A CN 103805166 A CN103805166 A CN 103805166A CN 201210457318 A CN201210457318 A CN 201210457318A CN 103805166 A CN103805166 A CN 103805166A
- Authority
- CN
- China
- Prior art keywords
- benzanthracene
- preparation
- organic luminescent
- dimethyl
- luminescent material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZFKJCOKHZYHEPC-UHFFFAOYSA-N CC(C)(c1ccc2)c(cc(cc3)-c(cc4)cc5c4[o]cc5)c3-c(cc3)c1c2c3-c1cc([o]cc2)c2cc1 Chemical compound CC(C)(c1ccc2)c(cc(cc3)-c(cc4)cc5c4[o]cc5)c3-c(cc3)c1c2c3-c1cc([o]cc2)c2cc1 ZFKJCOKHZYHEPC-UHFFFAOYSA-N 0.000 description 1
- HFHGHIOTHHAVBW-UHFFFAOYSA-N CC(C)(c1ccc2)c(cc(cc3)-c4cnc5c(nccc6)c6ccc5c4)c3-c(cc3)c1c2c3-c1cc(ccc2cccnc22)c2nc1 Chemical compound CC(C)(c1ccc2)c(cc(cc3)-c4cnc5c(nccc6)c6ccc5c4)c3-c(cc3)c1c2c3-c1cc(ccc2cccnc22)c2nc1 HFHGHIOTHHAVBW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
本发明涉及一种苯并蒽类有机发光材料及其制备方法和应用。解决现有蓝光材料无法满足工业化生产的问题。本发明提供的有机发光材料是一种基本骨架为苯并蒽类化合物，一含有3,9 -二溴-7,7-二甲基-7H-苯并蒽与含A取代基的硼酸为原料，通过Suzuki 偶联反应得到的，是一类成膜性能好，发光效率高的有机发光材料。该类有机发光材料的制备方法，反应溶剂改为常见的溶剂，便于操作，容易提纯，产率大幅度提高，降低了成本，使这系列化合物有了进一步开发应用的可能，能够满足工业化生产的需求。该类材料可作为有机发光材料、发光主体材料或传输材料，应用在电致发光器件上。The invention relates to a benzanthracene organic luminescent material and its preparation method and application. Solve the problem that the existing blue light materials cannot meet the needs of industrial production. The organic luminescent material provided by the present invention is a benzanthracene compound whose basic skeleton is a boronic acid containing 3,9-dibromo-7,7-dimethyl-7H-benzanthracene and A substituents as raw materials , obtained by Suzuki coupling reaction, is a kind of organic light-emitting material with good film-forming performance and high luminous efficiency. In the preparation method of this type of organic luminescent material, the reaction solvent is changed to a common solvent, which is convenient for operation and purification, greatly improves the yield, and reduces the cost, which makes it possible for this series of compounds to be further developed and applied, and can meet the requirements of industrial production. need. Such materials can be used as organic luminescent materials, luminescent host materials or transport materials in electroluminescent devices.
Description
Technical field
The invention belongs to organic photoelectrical material field, be specifically related to a kind of Benzanthracenes luminous organic material and its preparation method and application.
Background technology
The preparation of novel organic and high-molecular optical electric material and device design are very active fields in the world at present.Compared with liquid crystal flat panel display, the distinguishing feature such as organic and high molecule electroluminescent flat-panel screens (OLED and PLED) has active illuminating, non-angular dependency, good contrast, light, thin, energy consumption is low, has broad application prospects.Red Green Blue is the necessary requirement that realizes effective panchromatic demonstration.Wherein blue light material, due to wider energy gap, can be used as the doped body material of ruddiness and green light material.In addition, blue light, by look transfer medium technology (CCM), can also obtain ruddiness and green glow, realizes colour developing entirely.
At present, the colorimetric purity of blue-light device, the life-span, all lower than green device.No matter be to use pure small molecular blue light material, still general metal complexes blue light material, or even phosphor material is made the blue-light device obtaining and all cannot be overcome above-mentioned shortcoming.Existing blue light material also only can meet the application of certain fields.Being applied to the earliest electroluminescent material anthracene is exactly blue light material.But the easy crystallization of anthracene, is difficult for forming amorphous membrance, meanwhile, anthracene blue light material luminous efficiency is also lower.The blue-light device luminous efficiency of making of this material is not high yet.And preparation method's cost of anthracene blue light material is high, and productive rate and purity are not high, in building-up process, also can use more virose raw material, be difficult to carry out suitability for industrialized production.Therefore, research and develop efficient blue light material so that blue-light device can suitability for industrialized production, have great importance.
Summary of the invention
The present invention cannot meet the problem of suitability for industrialized production in order to solve existing blue light material, provide one to have higher photoluminescence efficiency, and cost is low, Benzanthracenes luminous organic material that productive rate and purity are high and its preparation method and application.
In order to solve the problems of the technologies described above, technical scheme of the present invention is specific as follows:
Benzanthracenes luminous organic material, the general structure of this material as the formula (1):
Wherein, A is C
8-C
18aromatic heterocyclic radical, C
9-C
15fused ring aryl or triarylamine.
Preferred Benzanthracenes luminous organic material of the present invention, wherein A is N-phenyl-2-carbazyl, 3-phenanthroline base, 5-benzofuryl, 2-phenanthryl, 9,9-dimethyl-2-fluorenyl, 5-indenyl or 2-naphthyl.
Benzanthracenes luminous organic material, it is any one in following 001-008 chemical structural formula:
Be exactly concrete structure formation more above, but this series compound does not limit to and these listed chemical structures.Every take formula (1) as basis, the A group for it compound of the simple transformation of the interior group of all scopes of front definition all should be included.
The preparation method of Benzanthracenes luminous organic material, this preparation method's concrete steps and condition are as follows:
(1) in molar ratio for 1:0.7 ~ 1.5 take 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene with containing the substituent boric acid of A;
(2) add again four (triphenyl phosphorus) palladium, sodium carbonate and solvent, four (triphenyl phosphorus) palladiums and 3,9-bis-bromo-7, the mol ratio of 7-dimethyl-7H-benzanthrene is 1:20 ~ 800, sodium carbonate and 3,9-bis-bromo-7, the mol ratio of 7-dimethyl-7H-benzanthrene is 1 ~ 4:1;
(3) degassed to reaction system;
(4) temperature of reaction system is risen to 70 ~ 100 ℃, back flow reaction 24 ~ 30 hours;
(5) cooling, suction filtration, washing, after being dried, obtains described Benzanthracenes luminous organic material.
In above-mentioned preparation method, the solvent adding in step (2) is tetrahydrofuran (THF).
In above-mentioned preparation method, in step (4), the temperature of reaction system is risen to 75 ~ 85 ℃.
In above-mentioned preparation method, the reflux time in step (4) is 27 ~ 29 hours.
Beneficial effect of the present invention:
1, a kind of basic framework provided by the invention is Benzanthracenes compound luminous organic material, owing to having introduced methyl, can increase the solvability of such luminous organic material, more easily processing, and film forming properties is good; Meanwhile, such luminous organic material, because the introducing of different substituents can change lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy level of this compounds, changes transition of electron energy level.So the emmission spectrum of this compounds has controllability, by regulating emmission spectrum can make this material can launch blue light, luminous efficiency also obviously improves; Therefore, luminous organic material of the present invention is the high performance electroluminescent material of a class, can meet the demand of suitability for industrialized production.
Particularly when A is N-phenyl-2-carbazyl, 3-phenanthroline base, 5-benzofuryl, triarylamine, 2-phenanthryl, 9, when 9-dimethyl-2-fluorenyl, 5-indenyl or 2-naphthyl, the luminous efficiency of the Benzanthracenes luminous organic material preparing in dilute solution is 95.9%, and the luminous efficiency in film is 57.5%.
2, the preparation method of Benzanthracenes luminous organic material provided by the invention, by optimizing reaction conditions, productive rate increases substantially, and productive rate can reach 92%; Reaction solvent changes common solvent into, and convenient operation is easily purified, and purified rear HPLC purity is greater than 98%; And reduced cost, and make this series compound have the possibility of further Application and Development, can meet the demand of suitability for industrialized production.
Particularly, when the temperature of reaction of reaction system is controlled at 75 ~ 85 ℃, reflux time is 27 ~ 29 hours, the Benzanthracenes luminous organic material preparing, and the luminous efficiency in dilute solution can reach 94.5%, and the luminous efficiency in film can reach 62.5%.
3, Benzanthracenes luminous organic material of the present invention is owing to having higher luminous efficiency, can be used as luminous organic material, luminous material of main part or transport material, be applied on electroluminescent device, data results by Application Example 1 shows, the blue-light device of making of material of the present invention, its luminous efficiency, brightness, driving voltage, there is good performance life-span and stability aspect, are very promising class electroluminescent organic materials.
Embodiment
Benzanthracenes luminous organic material provided by the invention is 3,9-bis-bromo-7 by containing, 7-dimethyl-7H-benzanthrene with obtain by Suzuki linked reaction the compound that general structure is formula (1) containing the substituent boric acid of A.Its synthetic route is as follows:
Embodiment 1: compound 001 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, N-phenyl-2-carbazyl boric acid 11.30g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 90 ℃, back flow reaction 24 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake is after water, ethanol and ether washing, oven dry obtains 3,9-bis-(N-phenyl carbazole bases)-7,7-dimethyl-7H-benzanthrene 30.32g, productive rate is more than 92%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 728.92; Test value is 728.90.Ultimate analysis: calculated value is C:90.63%; H:5.53%; N:3.84%; Test value is C:90.62%; H:5.54%; N:3.84%.
Embodiment 2: compound 002 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 3-phenanthroline ylboronic acid 15.63g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 100 ℃, back flow reaction 27 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-bis-(phenanthroline bases)-7,7-dimethyl-7H-benzanthrene 25.26g, productive rate is more than 93%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 600.71; Test value is 600.69.Ultimate analysis: calculated value is C:85.98%; H:4.70%; N:9.33%; Test value is C:85.96%; H:4.72%; N:9.32%.
Embodiment 3: compound 003 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 5-cumarone ylboronic acid 11.30g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 100 ℃, back flow reaction 30 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake is after water, ethanol and ether washing, oven dry obtains 3,9-bis-(benzofuryl)-7,7-dimethyl-7H-benzanthrene 19.40g, productive rate is more than 90%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 476.56; Test value is 476.54.Ultimate analysis: calculated value is C:88.21%; H:5.08%; O:6.71%; Test value is C:88.20%; H:5.07%; O:6.72%.
Embodiment 4: compound 004 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, triarylamine boric acid 20.17g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 75 ℃, back flow reaction 27 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-bis-(triarylamine)-7,7-dimethyl-7H-benzanthrene 29.75g, productive rate is more than 90%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 730.94; Test value is 730.95.Ultimate analysis: calculated value is C:90.38%; H:5.79%; N:3.83%; Test value is C:90.36%; H:5.80%; N:3.84%.
Embodiment 5: compound 005 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 2-phenanthryl boric acid 15.49g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 85 ℃, back flow reaction 29 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-bis-phenanthryl-7,7-dimethyl-7H-benzanthrene 25.1g, productive rate is more than 93%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 596.76; Test value is 596.78.Ultimate analysis: calculated value is C:94.60%; H:5.40%; Test value is C:94.62%; H:5.38%.
Embodiment 6: compound 006 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 9,9-dimethyl-2-fluorenyl boric acid 16.61g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 95 ℃, back flow reaction 25 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-bis-fluorenyl-7,7-dimethyl-7H-benzanthrene 26.00g, productive rate is more than 90%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 628.84; Test value is 628.82.Ultimate analysis: calculated value is C:93.59%; H:6.41%; Test value is C:93.60%; H:6.42%.
Embodiment 7: compound 007 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 5-indenyl boric acid 11.16g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 100 ℃, back flow reaction 24 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-bis-indenyl-7,7-dimethyl-7H-benzanthrene 19.23g, productive rate is more than 90%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 472.62; Test value is 472.60.Ultimate analysis: calculated value is C:94.03%; H:5.97%; Test value is C:94.05%; H:5.99%.
Embodiment 8: compound 008 synthetic
Concrete synthetic route is shown below:
By 3,9-bis-bromo-7,7-dimethyl-7H-benzanthrene 18.18g, 2-naphthyl boric acid 12.0g, sodium carbonate 20g, tetrahydrofuran (THF) 250ml and water 125ml add there-necked flask, degassed, add four (triphenyl phosphorus) palladium 0.9g, be warming up to 90 ℃, back flow reaction 26 hours, be cooled to room temperature, separate out after solid suction filtration, filter cake, after water, ethanol and ether washing, is dried and is obtained 3,9-dinaphthyl-7,7-dimethyl-7H-benzanthrene 20.21g, productive rate is more than 90%, and HPLC purity is greater than 98%.Mass spectrum: calculated value is 496.64; Test value is 496.62.Ultimate analysis: calculated value is C:94.32%; H:5.68%; Test value is C:94.30%; H:5.70%.
Application example 1
The ito glass substrate that it is formed with to 1000 thickness in the above, is placed on the ultrasonic middle cleaning 30 minutes of washings, then uses distilled water ultrasonic cleaning 10 minutes twice.After distilled water wash, use respectively Virahol, toluene, acetone, ethanol difference ultrasonic cleaning 30 minutes, then dry.Finally put into plasma washing machine, use oxygen plasma cleaning base plate 5 minutes, send into vacuum evaporation equipment and process.
By NPB, the sample of preparation in embodiment 1, AlQ, LiF, Al respectively evaporation, to device, goes into object construction device: [sample (30nm)/AlQ (20nm)/LiF (the 5nm)/Al (10nm) of preparation in ITO/NPB (20nm)/embodiment 1].Organism velocity of evaporation is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum keep is 10
-5vacuum tightness below pa.
The test result that the sample making of preparing in embodiment 1 obtains device 001 is cut-in voltage 4v, and high-high brightness is 3600cd/m
2, under 10v voltage, observing efficiency is 27Lm/w, chromaticity coordinates (CIE) value is x:0.14; Y:0.14, obtains a blue device, and life-span transformation period of device is 20000 hours.
The sample making of embodiment 2 ~ 8 preparation becomes device 002 ~ 008, and its structure is identical with the device architecture of embodiment 1 sample making, and test result is as table 1:
The device performance test of the sample making of table 1 embodiment 2 ~ 8
The luminous efficiency of the sample compound of table 2 embodiment 1 ~ 8 preparation
| Sample | Luminous efficiency in dilute solution | Luminous efficiency in film |
| Embodiment 1 | 98% | 55% |
| Embodiment 2 | 97% | 57% |
| Embodiment 3 | 95% | 58% |
| Embodiment 4 | 95% | 62% |
| Embodiment 5 | 94% | 63% |
| Embodiment 6 | 96% | 54% |
| Embodiment 7 | 97% | 55% |
| Embodiment 8 | 95% | 56% |
Can find out from the data of table 2, the luminous efficiency of the Benzanthracenes luminous organic material that embodiment 1 ~ 8 prepares in dilute solution is 95.9%, luminous efficiency in film is 57.5%, show that this Benzanthracenes compound has high luminous efficiency, can be used as luminescent material or luminous material of main part and transport material, be applied in electroluminescent device.According to application example 1, the sample of preparation in embodiment 1 ~ 8 is used for making blue-light device simultaneously, the performance test results of its device is as shown in table 1: by data test and comparison, we find that this compounds is the electroluminescent organic material of excellent property, particularly, as the good luminous material of main part of Performance Ratio and transport material, it is a very promising class electroluminescent organic material.
Obviously, above-described embodiment is only for example is clearly described, and the not restriction to embodiment.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here without also giving exhaustive to all embodiments.And the apparent variation of being extended out thus or variation are still among the protection domain in the invention.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210457318.3A CN103805166B (en) | 2012-11-14 | 2012-11-14 | Benzanthracenes luminous organic material and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210457318.3A CN103805166B (en) | 2012-11-14 | 2012-11-14 | Benzanthracenes luminous organic material and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103805166A true CN103805166A (en) | 2014-05-21 |
| CN103805166B CN103805166B (en) | 2015-12-02 |
Family
ID=50702568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210457318.3A Active CN103805166B (en) | 2012-11-14 | 2012-11-14 | Benzanthracenes luminous organic material and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103805166B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104017586A (en) * | 2014-05-29 | 2014-09-03 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104017585A (en) * | 2014-05-29 | 2014-09-03 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| WO2016126423A3 (en) * | 2015-02-03 | 2016-12-01 | E I Du Pont De Nemours And Company | Electroactive materials |
| CN108047130A (en) * | 2017-12-05 | 2018-05-18 | 李现伟 | Benzanthracenes electroluminescent organic material, luminescent device and display |
| US10193073B2 (en) * | 2014-06-05 | 2019-01-29 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting device including the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998039287A1 (en) * | 1997-03-05 | 1998-09-11 | Trimeris, Inc. | Benzanthrone compounds and antiviral uses thereof |
| WO2010038956A2 (en) * | 2008-09-30 | 2010-04-08 | Daejoo Electronic Materials Co., Ltd. | Novel aromatic derivatives and organic electroluminescent device comprising same |
| WO2011126224A1 (en) * | 2010-04-06 | 2011-10-13 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
-
2012
- 2012-11-14 CN CN201210457318.3A patent/CN103805166B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998039287A1 (en) * | 1997-03-05 | 1998-09-11 | Trimeris, Inc. | Benzanthrone compounds and antiviral uses thereof |
| WO2010038956A2 (en) * | 2008-09-30 | 2010-04-08 | Daejoo Electronic Materials Co., Ltd. | Novel aromatic derivatives and organic electroluminescent device comprising same |
| WO2011126224A1 (en) * | 2010-04-06 | 2011-10-13 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Non-Patent Citations (1)
| Title |
|---|
| 余明新等: "苯并[de]蒽-7-酮类叔芳胺的合成及其发光性能的研究", 《有机化学》 * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104017586A (en) * | 2014-05-29 | 2014-09-03 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104017585A (en) * | 2014-05-29 | 2014-09-03 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104017585B (en) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104017586B (en) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| US9382478B2 (en) | 2014-05-29 | 2016-07-05 | Boe Technology Group Co., Ltd. | Liquid crystal composition and methods for the preparation thereof |
| US10193073B2 (en) * | 2014-06-05 | 2019-01-29 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting device including the same |
| KR20170109586A (en) * | 2015-02-03 | 2017-09-29 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Electroactive material |
| CN107250087A (en) * | 2015-02-03 | 2017-10-13 | E.I.内穆尔杜邦公司 | Electroactive material |
| WO2016126423A3 (en) * | 2015-02-03 | 2016-12-01 | E I Du Pont De Nemours And Company | Electroactive materials |
| KR102238701B1 (en) * | 2015-02-03 | 2021-04-08 | 주식회사 엘지화학 | Electroactive material |
| CN107250087B (en) * | 2015-02-03 | 2022-01-18 | 株式会社Lg化学 | Electroactive material |
| US11683979B2 (en) | 2015-02-03 | 2023-06-20 | Lg Chem, Ltd. | Electroactive materials |
| US12232413B2 (en) | 2015-02-03 | 2025-02-18 | Lg Chem, Ltd. | Electroactive materials |
| CN108047130A (en) * | 2017-12-05 | 2018-05-18 | 李现伟 | Benzanthracenes electroluminescent organic material, luminescent device and display |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103805166B (en) | 2015-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103833507B (en) | A series of electroluminescent organic materials and preparation method and application | |
| CN102925139A (en) | Organic light-emitting material with excellent performance and preparation method thereof | |
| CN103204880B (en) | A kind of organophosphorus luminescent material, its preparation method and the organic electroluminescence device be made up of it | |
| CN103805165A (en) | Benzanthracene organic electroluminescent material, and preparation method and application thereof | |
| CN110526901A (en) | An organic luminescent material and its application in the preparation of organic electroluminescent devices | |
| CN103805166A (en) | Benzanthracene organic luminescent material, and preparation method and application thereof | |
| CN103113289B (en) | Organic electroluminescent material containing benzanthracene derivative and preparation method of organic electroluminescent material | |
| CN111662190A (en) | Organic compound containing pyrene or aza-pyrene and application thereof | |
| CN103664906A (en) | 6, 6-dimethyl-6H- benzo [cd] pyrene derivative and application thereof | |
| CN109503427B (en) | A D-A type organic blue fluorescent material and its preparation method and application | |
| CN111675714B (en) | Organic electroluminescent compound with balanced carrier transmission performance and application thereof | |
| CN110467626B (en) | A novel spiro structure compound and its application in OLED devices | |
| CN109608403B (en) | A class of anthracene-tetraphenylene-based organic blue-light small molecules and their applications in the preparation of undoped organic electroluminescent devices | |
| CN103805167B (en) | Organic blue luminescent material and its preparation method and application | |
| CN103102877B (en) | Silicon-containing organic luminescent material as well as preparation method and application of organic luminescent material | |
| CN102924367A (en) | Benzanthracene organic light-emitting material and preparation method thereof | |
| CN104650066A (en) | Preparation of green light material, as well as organic light emitting device of green light material | |
| CN103834381B (en) | Siliceous Benzanthracenes luminous organic material and its preparation method and application | |
| CN103102299B (en) | A kind of benzanthrene derivative, its preparation method and the electroluminescent organic material be made up of it | |
| CN111377943A (en) | Quinary heterocyclic organic compound and application thereof | |
| CN113735831B (en) | Compound, intermediate, preparation method of compound and intermediate, and organic electroluminescent device | |
| CN118561878A (en) | Composition containing heterocyclic compound | |
| CN103045231A (en) | Aryl-biquinoline iridium-complex organic phosphorescent material, preparation method and applications of aryl-biquinoline iridium-complex organic phosphorescent material | |
| CN103113281A (en) | Benzanthracene efficient organic light emitting material and preparation method | |
| CN103804408A (en) | Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |